Lewis acid catalyzed acylation reactions: scope and limitations

Kusum L. Chandra, P. Saravan, Rajesh K. Singh and Vinod K. Singh*

*Department of Organic Chemistry, Indian Institute of Technology, Kanpur 208 016, India, Email: vinodksiitk.ac.in

K. L. Chandra, P. Saravan, R. K. Singh, V. K. Singh, Tetrahedron, 2002, 58, 1369-1374.

DOI: 10.1016/S0040-4020(01)01229-7

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Abstract

Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu(OTf)₂ was very efficient in catalyzing the reaction under mild conditions in CH₂Cl₂. The selectivity for acylation of primary or secondary alcohols over tertiary ones is discussed.

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proposed mechanism

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Key Words

acylations, acetic acid esters, thioesters, alcohols, thiols, phenols, sugars, copper triflate, acetic anhydride

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ID: J72-Y2002-1020